A stable analog of PGF2α 2-glyceryl ester
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17-phenyl trinor Prostaglandin F2α serinol amide

Item No. 10004237

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]cyclopentyl]-N-[2-hydroxy-1-(hydroxymethyl)ethyl]-5-heptenamide
CAS Number
1175838-84-2
Synonyms
  • Bimatoprost serinol amide
  • 17-phenyl trinor PGF2α-SA
Molecular Formula
C26H39NO6
Formula Weight
461.6
Purity
≥98%
Formulation (Request formulation change)
A 10 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 10 mg/mlEthanol: 10 mg/mlPBS (pH7.2): 0.5 mg/ml
SMILES
O[C@H](/C=C/[C@@H]1[C@@H](C/C=C\CCCC(N([H])C(CO)CO)=O)[C@@H](O)C[C@H]1O)CCC2=CC=CC=C2
InChi Code
InChI=1S/C26H39NO6/c28-17-20(18-29)27-26(33)11-7-2-1-6-10-22-23(25(32)16-24(22)31)15-14-21(30)13-12-19-8-4-3-5-9-19/h1,3-6,8-9,14-15,20-25,28-32H,2,7,10-13,16-18H2,(H,27,33)/b6-1-,15-14+/t21-,22+,23+,24-,25+/m0/s1
InChi Key
FQGNKSXLEDAGFC-LSLURRSKSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $81

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    5 mg

    $357

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    10 mg

    $633

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    50 mg

    $2,756

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    Product Description

    2-Arachidonyl glycerol (2-AG) exhibits cannabinoid agonist activity at the central cannabinoid (CB1) receptor, is an important endogenous monoglyceride species, and is thus considered to be the natural ligand for the CB1 receptor.1,2 2-AG can also be metabolized by COX-2 to form prostaglandin (PG) 2-glyceryl esters.3 These 2-glyceryl esters rapidly equilibrate to form 90:10 mixtures favoring the more stable 1-glyceryl ester. 17-phenyl trinor Prostaglandin F2α serinol amide (17-phenyl trinor PGF2α-SA) is a stable analog of PGF2α 2-glyceryl ester incorporating an activity-enhancing 17-phenyl substitution. The biological activity of 17-phenyl trinor PGF2α-SA has not yet been determined.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sugiura, T., Kodaka, T., Kondo, S., et al. Is the cannabinoid CB1 receptor a 2-arachidonoylglycerol receptor? Structural requirements for triggering a Ca2+ transient in NG108-15 cells. J. Biochem. 122(4), 890-895 (1997).

    2. Kondo, S., Kondo, H., Nakane, S., et al. 2-Arachidonoylglycerol, an endogenous cannabinoid receptor agonist: Identification as one of the major species of monoacylglycerols in various rat tissues, and evidence for its generation through Ca2+-dependent and -independent mechanisms. FEBS Lett. 429(2), 152-156 (1998).

    3. Kozak, K.R., Crews, B.C., Morrow, J.D., et al. Metabolism of the endocannabinoids, 2-arachidonylgycerol and anandamide, into prostaglandin, thromboxane, and prostacyclin glycerol esters and ethanolamides. The Journal of Biological Chemisty 277(47), 44877-44885 (2002).